HomeEntertainmentMusic’90s Country: Toby Keith’s Top 5 Music Videos of the Decade

’90s Country: Toby Keith’s Top 5 Music Videos of the Decade

by Matthew Wilson
Photo credit: Tim Mosenfelder/Getty Images

Toby Keith has been around the country music block. The singer hit the country music industry back in the 1990s with his brash style. But whether it’s a sad song or a party anthem, Keith knows how to invoke emotion, especially with his music videos.

Outsider took a look back at some of his biggest songs from the ’90s. Here are Toby Keith’s Top Five Music Videos.

5. Toby Keith Has a Party in ‘A Little Less Talk And A Lot More Action’

The music video for this country is simpler than some of Toby Keith’s other efforts, but no less fun. The country singer is throwing a honkey tonk party amid a sea of cowboy hats. Like the audience, the hit song will get listeners up off their feet and embracing their inner country music.

What makes the music video so successful is its focus on the crowd. Viewers can see the effect Keith’s music can have during the best of times. After-all, the tune is a rallying cry to live it up and party, among other things. Never let it be said that Keith doesn’t know how to have a good time.

4. Keith Sings of Love in “Does That Blue Moon Ever Shine On You?”

Toby Keith is feeling the blues quite literally in this 90’s love ballad. “Does That Blue Moon Ever Shine on You?” proves the singer can stand among the best love songs of that era. And the music video for the tune certainly sets a mood. With its soft glow, blue tones, and crossfade, the music video creates the feeling of one of those gloomy nights.

The video matches Keith’s sad melody, creating a lonesome feeling of those twilight hours. The singer laments loss love during a time he really should be in bed asleep. For those who’ve experienced a similar situation, never have those night time hours felt so blue.

3. “Who’s That Man” Shows Toby Keith’s Soft Side

“Who’s That Man” is another song that shows off the singer’s sensitive side. This tune explores the point of view of a man post-divorce. He watches as his ex-wife moves on to someone new. The narrator ponders wistfully on the man who’s taken on the role of her husband and also father to their children. He feels like the life he wanted has been stolen from him.

The music video films scenes of domestic bliss in a soft-glow common for the decade. It creates a reality that seems storybook and too good to be true. The dream-like nature is contrasted with Keith’s narrator driving down the road sadly. The song became Keith’s second No. 1 hit.

2. “Should’ve Been a Cowboy” Is a Classic

What’s country music without a little Old West? “Should’ve Been a Cowboy” was the song that started it all. Featured as the debut single on Keith’s debut album, the tune introduced country music to its next biggest star. Released in 1993, the tune also became Keith’s first No. 1 hit.

The music video leaned heavily into its western roots. It contrasts a singing Keith with a sepia colored landscape. As a cowboy, Keith does it all. From riding a horse to participating in a duel, the country singer appears to have a lot of fun embracing his inner cowboy.

1. Toby Keith is At His Best in ‘How Do You Like Me Now?!’

They say the best revenge is a good life. Released in 1999, Keith closed out the decade on top with this ultimate revenge tune. This No. 1 hit went out to all those who felt overlooked in life and dreamed of becoming successful. Who wouldn’t want to return to their high school or old flame as big hot shot?

The music video features peak Toby Keith, at his most cocky. The country singer is all kinds of hilarious as he revels in the fact that he’s now too good for an old crush. Through the entire process, he carries a devilish grin and arrogance that enhances the song and its message.